Chlorosuccinimide → 6-fluoro-N,1-dihydroxy-3,3-dimethyl-1,3-dihydro benzo[c][1,2]oxaborole-5-carbimidoyl chloride

HRID 532237Notes

Reaction equation

[F:1][C:2]1[C:3]([CH:14]=[N:15][OH:16])=[CH:4][C:5]2[C:9]([CH3:11])([CH3:10])[O:8][B:7]([OH:12])[C:6]=2[CH:13]=1.C1C(=O)N([Cl:24])C(=O)C1>CN(C=O)C>[F:1][C:2]1[C:3]([C:14]([Cl:24])=[N:15][OH:16])=[CH:4][C:5]2[C:9]([CH3:11])([CH3:10])[O:8][B:7]([OH:12])[C:6]=2[CH:13]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of the crude compound 6-fluoro-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde oxime (205 mg, 0.92 mmol) in DMF (4.0 mL) at rt was added NCS (147 mg, 1.1 mmol). The reaction mixture was stirred at 45° C. for 3 h. The mixture was cooled to rt, poured into ice-water and extracted with DCM (60 mL×3). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude compound 6-fluoro-N,1-dihydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbimidoyl chloride as colorless oil. It was used in next step without further purification.

Workup

temperatureThe mixture was cooled to rt
extractionextracted with DCM (60 mL×3)
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0fd90ebd42a8440a800d6669adbdb3cb
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853186B2

Reaction notes

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